1. Field of the Invention
This invention relates to the field of new derivatives of 3-isothiazolones, their preparation, and their use in controlling living organisms.
2. Description of the Prior Art
3-Isothiazolones have generated high commercial interest as microbicides to prevent spoilage caused by microorganisms in a large number of aqueous and nonaqueous products subject to such spoilage. 3-Isothiazolones are highly effective microbicides (as used herein, "microbicides" includes bactericides, fungicides, and algaecides and microbicidal activity is intended to include both the elimination of and inhibition or prevention of growth of microbial organisms such as bacteria, fungi, and algae) and are useful in a broad range of applications.
Lewis et al., U.S. Pat. Nos. 3,761,488; 3,544,580; 3,835,150; 3,706,757; 3,755,224; and 4,105,431, all assigned to Rohm and Haas Co., the same assignee as the present invention, disclose 3-isothiazolone compounds.
U.S. Pat. No. 3,835,150 to Lewis, also assigned to Rohm and Haas Co., discloses certain acrylic isothiazolonyl derivatives. Lewis discloses the reaction of certain 3-hydroxyisothiazoles with acetylenic compounds, such as methyl propiolate, propiolnitrile, N,N-dimethylpropiolamide, and propiolic acid in the presence of a base catalyst such as triethyl amine or a quaternary ammonium hydroxide. While this patent discloses other potential reactions, only a few specific products are provided. Compound A below (compound 16 disclosed in Lewis '150 at Table I), as well as the other possible products listed in Example 22 of the '150 patent, result from the reaction occurring at the oxygen, not at the nitrogen of the 3-hydroxyisothiazoles. ##STR2##
Lewis '150 further discloses the reactions of certain active halogen compounds with 3-hydroxyisothiazoles. Of particular note are the reactions of .beta.-haloacrylates, .beta.-haloacrylamides, and .beta.-haloacrylonitrile with 3-hydroxyisothiazoles to yield compounds of structure B below, wherein X is halogen and Z is alkoxy, amino or nitrile. The compounds exemplified in this patent show reaction at the oxygen only; no compounds corresponding to reaction at the nitrogen of the 3-hydroxyisothiazoles are reported. ##STR3##
U.S. Pat. No. 4,105,431 to Lewis, also assigned to Rohm and Haas Co., discloses reacting vinyl acetate with a 3-hydroxyisothiazole to give a vinyl substituted isothiazolone, compound C below. The patent further discloses that mercuric salts can be advantageously used to catalyze the reaction. ##STR4## Also disclosed in this patent is the reaction of 3-hydroxyisothiazole with an appropriate haloalkene or haloalkyne to give the 2-alkenyl- or 2-alkynyl-3-isothiazolone, respectively. This reaction is that of a simple alkylation of the 3-hydroxyisothiazole nitrogen. An acid accepting base, such as a metal hydride or metal hydroxide, is normally used to catalyze this reaction.